Seasonal gigs can bring extra cash, career changes — and job offers

Want to sample Michelin star food, watch Madonna strike a pose or see Yankees captain Aaron Judge slam a home run?

These are all perks that Zane Michael, 25, has enjoyed working as a brand ambassador at local events. He boosts his earnings with summer side hustles while working at Trader Joe’s in Chelsea and acting.

“Summertime is full of opportunity,” said the Bushwick resident, whose typical gigs involve getting revelers to sign up in exchange for freebies. “Pride Month [June] is one of the most lucrative months, considering the city is gripped with celebration and unity.”

Zane Michael, 25, has enjoyed working as a brand ambassador at local events.

Five summers ago, Michael applied to booking agencies Assist Marketing and Brand Allure. He interviewed, waited out a vetting process that included background checks and was cleared to apply to the gigs they posted.

He’s since attended events such as the Governors Ball and US Open tennis, and now that he has experience and has forged connections with brands such as Chase, BMW and Bank of America, marketing teams sometimes contact him directly for gigs.

Responsibilities don’t require meeting quotas, so he focuses on initiating friendly conversations.

“Managers don’t expect results from interactions; they expect effort,” said Michael.

He recommends signing up for tournaments for steadier work. “If it’s a concert or sporting event, you just work for that day and have to apply for more gigs. On the PGA tour, you could work two weeks consistently. Just starting out, you might get $20 to $25 an hour.”

Flexibility is key to navigating roles and the elements. “Sometimes you’re at Pier 17 walking around the seaport, other times you’re lugging tables and water coolers through mud in Central Park for a running club,” said Michael. “Don’t expect glamour, but appreciate it if it finds you.”

“Summertime is full of opportunity,” said Michael.

Prior to 2019, marketing wasn’t on his radar, but thanks to these gigs, he would now “absolutely love” to work in marketing for a Broadway theater.

Michael isn’t alone in leaning into summer side hustling. According to 2023 data from personal finance site Bankrate, nearly 39% of US adults have a side hustle, with one in three people needing the money for daily living expenses. And it helps: Side hustlers earn an average of $810 extra per month.

“Summer hustles can be great for earning additional cash,” said Cynthia Pong, JD, founder and CEO of Embrace Change, a Harlem-based career coaching and training firm. “We should all be building multiple income streams,” she said. Other perks are “meeting new people, having a change of pace, learning or strengthening a skill set, as well as spending time in nature or outdoors if the position provides the opportunity for that.”

A big win is if you’re able to do something you love while boosting both your bank account and endorphins.

That’s what Bedford-Stuyvesant resident Stephanie Loehr has in store this summer.

She makes a hard stop every Thursday night at 6 p.m. in her role as director of planning at luxury fashion brand Alexander Wang. She then sprints to Pier 40 at Hudson River Park. Here, she’s a referee for NYC Footy, a coed soccer league. After officiating three or four games, by about midnight, she calls it a day, having run between five and seven miles during the matches.

“If I wasn’t doing this, I would swap it out with some other exercise. I’m fortunate that I can have a side hustle that is a hobby,” said Loehr who played soccer in high school and college.

She’s also kicking around new work skills.

“As a ref, you’re forced to be decisive, to be in charge and at the same time enable the flow of the game,” said Loehr. “If you’re keeping a friendly demeanor with people regardless of how they’re reacting, that can diffuse situations, which I think could be a good life skill.”

“I just could never fully pull myself away from being on boats,” said Field.

NYC Footy plans to hire 70 to 90 referees this summer at a starting hourly rate of $25. Loehr earns approximately $1,000 a month during the season (which includes duties on another weeknight and some weekends).

Loehr found her way into the role five years ago, when, while playing Footy soccer, she asked a referee about officiating.

If you don’t have an “in,” network, peruse summer opportunities online and apply to seasonal gigs at pools, camps, country clubs, hotels and restaurants.

As captain, after being asked many times to officiate weddings, Field now has another side hustle — as a marriage officiant.

Remember to highlight any skills that transfer to the job, and negotiate pay, said Barbara Spitzer, founder of Two Rivers Partners, a human capital and strategy execution firm downtown.

“Do not sell yourself short,” she said. “Any gig, even if you mowed lawns on the country club golf course, can bring out the power skills you deployed, such as the ability to create a positive customer experience as you interact with members out on the green.”

Additionally, if you already have the foot in the door of a seasonal gig, a full-time job might find you. Adrian Klaphaak, career coach and founder of A Path That Fits, in Park Slope, said, “Do amazing work and build meaningful relationships with your co-workers and clients. If you are adding value to the organization and well-liked by everyone, they will do everything possible to keep you around.”

This is what happened to Capt. Cait Field, 41, general manager at Classic Harbor Line, a year-round NYC fleet of motor yachts and schooners.

The Brooklyn resident grew up sailing small boats in Long Island and started working for Classic Harbor Line to help get through grad school, where she was pursuing a Ph.D. in biopsychology.

“Everyone should stay open to what their career may look like and how it may evolve and change,” Field said.

During summer weekends, on top of her full-time job as Freshkills Park manager at the NYC Department of Parks & Recreation, she worked with the cruise line, and while she enjoyed working full-time in the sciences, she couldn’t shake the maritime world.

“I just could never fully pull myself away from being on boats,” said Field, who joined the company full-time two years ago. “It’s always what I’ve most loved. Everyone should stay open to what their career may look like and how it may evolve and change.”

As captain, after being asked many times to officiate weddings, Field now has another side hustle — as a marriage officiant. After being asked many times, “I thought, ‘Well, why not?’” she said.

As you stay open to blossoming paths, keep logistics top of mind: Employers may set you up as a W-9 contractor or W-2 part-time employee, so know the tax and legal implications. Also ensure you’re not stretched too thin, since seasonal work can accumulate faster than a New York minute.

“Double-check your contract with your full-time employer,” said Susan Weil, co-CEO of Midtown-based global career advisory firm Weil & Wein and JobTreks, a free, curated database of companies. “Some employers limit your ability to work at other places.”

And advice if you’re going to be on your feet all day: “Stretch, soak your feet, always wear sneakers,” said Zane Michael. “If the event uniform demands dress shoes, orthopedic soled shoes can really help. Walking around Madison Square Garden for about six hours, they saved my life.”

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